Welcome to the second blog in the“Molecules of Note” series on Malvern’s Materials Talks blog site. Last time we extolled the importance of (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid, better known as Lipitor.
This month’s molecule of note is Galanthamine, a drug used to treat Alzheimer’s with an unusual derivation, being synthesized from the snowdrop flower. According to one historical account, a Bulgarian pharmacologist was visiting a rural area, on the outskirts of Sofia, around 1950 when he saw people rubbing snowdrops on their foreheads to ease headaches, and his curiosity was aroused. It is certainly fact that in 1952 Russian scientists isolated galanthamine (systematic IUPAC name, (4aS,6R,8aS)- 5,6,9,10,11,12- hexahydro- 3-methoxy- 11-methyl- 4aH- benzofuro[3a,3,2-ef]  benzazepin- 6-ol) from Caucasian snowdrops (Galanthus woronowii) and within a few years it was being used in anaesthesiology as a curare reversal agent and also in the treatment of poliomyelitis. In its pure form it is a white powder.
There is not enough plant-derived galanthamine available, so chemical synthesis is increasingly being looked at as an option. Galanthamine is available as a commercial pharmaceutical under the brand name Razadyne® ER in opaque hard gelatin extended-release capsules. Inactive ingredients include gelatin, diethyl phthalate, ethylcellulose, hypromellose, polyethylene glycol, titanium dioxide and sugar spheres (sucrose and starch).
With annual sales reportedly at $130M this pharmaceutical is not a block buster but the interesting origin of the active molecule and the disease it helps to cure make it certainly worthy of note.
Do you have a favorite molecule? Do you think this one can be beaten? Let us know.